


Do It Right

by hit_the_books



Category: Supernatural
Genre: Alternate Universe - High School, Anal Fingering, Bisexual Dean Winchester, Castiel/Dean Winchester First Time, Christmas, Christmas Party, Christmas Smut, First Time, First Time Bottom Dean, First Time Bottoming, History Teacher Castiel, M/M, Teacher Dean, Top Castiel, Top Castiel/Bottom Dean Winchester
Language: English
Status: Completed
Published: 2016-12-24
Updated: 2016-12-24
Packaged: 2018-09-11 19:59:40
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 1,615
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/9009841
Author URL: https://archiveofourown.org/users/hit_the_books/pseuds/hit_the_books
Summary: It's winter break, school's out, and Dean's having a meal with some of his faculty colleagues before they go their separate ways for Christmas. A few drinks and an embarrassing confession later: Dean finds out why the new history teacher has been staring at him all semester.





	

**Author's Note:**

> This is based on a conversation I overheard at my own work Christmas party the other week. Whether or not the parties involved went on to enact any of this: I plan on never knowing.

Three beers and a triple cheeseburger in, Dean Winchester decides he’s having a good time at the end of semester Christmas party/meal that Charlie organized. Looking around his colleagues gathered in Lafitte’s Bar and Grill, Dean acknowledges that he’s the most relaxed and happy he’s been in weeks. Okay, so maybe it has something about the high school being closed for winter break and finally having some time to himself. 

Or maybe it has something to do with the way the new history teacher, Castiel Novak—who’d joined them in the fall—keeps glancing over at Dean with a look that’s anything but professional. The same look that Dean thought he’d been imagining for months. 

“Deano, c’mon, you must have tried it,” Gabriel says, snapping Dean’s attention back to his other colleagues. He has no idea what the music teacher is talking about. 

“Come again?” Dean asks, taking a sip of his fourth beer. 

“Have you ever had anal?” 

Dean splutters, some beer going up his nose and burning. Charlie, Gabriel, Garth, Jo, Victor, Eileen and Castiel all look at Dean. Everyone else is smirking, but not Castiel—no he retains his intense gaze that is demanding an answer to a different question that Dean doesn’t know he’s being asked. 

Recovering himself, Dean answers, “Some girl I was with once slipped her finger in there, but I didn’t think much of it. So not an anal guy.” _Wait, why the hell did I just tell them all that?!_ Dean looks at the empty beer bottles beside him and then an empty shot glass. He’d drunk more than he’d realized. 

“Ha!” Gabriel slaps Dean on the back. “Okay, so you’re not an anal guy…” Gabriel turns to the rest of the group continues to ask awkward questions of the rest of their party. 

“She obviously didn’t do it right,” Castiel growls low, but no one else seems to notice his comment. No one but Dean, who feels like Castiel’s blue eyes are pinning him to his seat, making it impossible for him to move or look anywhere else. 

_Christ_ , Dean thinks to himself, finally tearing his gaze away, cheeks red as he discreetly shifts himself in his pants. He starts to reconsider every look, every word, he’s shared with Castiel since the start of the school year. The brush of hands in the teachers’ lounge each time they went for the same donut during Monday morning meetings. Bumping into each other in the parking lot at the end of the day. Always finding each other’s eyes during lunch breaks when they’re sat in the teachers’ lounge as opposed to eating in their offices. 

Something has been building between them and serving it up with a mix of booze was making it harder and harder to avoid. Excusing himself, Dean heads for the restroom. He stands in front of a sink, turns on the faucet and splashes cold water onto his face. The chill of the water cleanses some of the boozy haze he’s been running under. 

The door to the restroom eases open and Castiel stalks in. Wiping his face with a paper towel, Dean turns to face Castiel and quietly gulps as he drinks in the man’s mussed up hair, flushed face and startling eyes. Dean knows Castiel has drunk less than him, so he’s surprised when his colleague steps into his space, bringing his face an inch away from Dean’s. Castiel’s white dress shirt visibly rises up and down as if he’s just run into the restroom. 

“Look, I—” Dean starts. 

Castiel doesn’t give Dean a chance to finish talking, instead bridging that last bit of distance between them and pressing their lips together. The kiss starts soft and then Dean leans into it, eager and hungry for answers to whatever’s been going on between them. Hands snake around Dean’s waist, rucking up his dress shirt, and then slide down to cup the clefts of his ass. Wetly kissing until they need air, Dean pulls away as far as Castiel’s hands will let him. 

“Fuck, Cas,” Dean says, the nickname coming naturally to him now. 

“That’s the plan,” Cas growls and then yanks Dean out of the rest room. The two of them pay up for their end of the drinks and food, grab their coats and head out into the night, the rest of their party stunned into silence by their wake. A woman every Friday Dean has left with a man, and Dean has never felt so excited in his life. 

Cas only lives two blocks from the bar, so they walk back to his apartment. They stop three times in the mouths of alleyways to kiss each other stupid, their breaths huffing out around them in the frosty air. Eventually they reach Castiel’s apartment building and Cas drags Dean inside. They pound their way up to Castiel’s apartment and manage to make it inside without any of Castiel’s neighbors yelling at them for banging into walls or blocking hallways. 

“We need to get naked,” Cas points out once the door closes behind them. He doesn’t wait for Dean to reply, instead reaching out for Dean’s jacket, fingers deftly shedding Dean’s many layers. Helping Cas with his clothes, the hallway come living room is awash with their clothing as Cas pulls Dean into his bedroom. 

Dean’s thrown down onto Castiel’s bed, anticipation curling in his gut as Cas pulls out something from a drawer. Seeing the lube, Dean’s brain takes a moment to catch up with what’s happening and he lets out a shaky breath. 

“Dean, if you don’t want me to do something, just tell me, okay?” 

Nodding, Dean holds out a hand towards Cas. “Show me how it’s done right?” 

Biting his bottom lip, Cas nods. “Roll onto your side.” 

“Dude, I am so not the little spoon,” Dean scoffs. 

“You are tonight, Winchester.” Cas climbs onto the bed and eases Dean onto his side. Complying, Dean lays out and hears the sound of a lube bottle being popped open. Cas pushes an arm under his hips, hand brushing over Dean’s more than ready cock. Castiel’s other hand snakes past Dean’s crack and a lubed finger starts to circle Dean’s hole, making him shiver. 

A whimper escapes Dean and Cas wraps Dean’s cock with his fist. Dean can’t help pushing back against Cas as the man strokes him. “FUCK!” Dean shouts in surprise as Castiel’s finger pushes past that first ring of muscle in his ass. There’s a slight niggling burn that’s quickly eased away by the attention on his cock. 

“I thought I’d die of starvation before this moment,” Cas whispers into Dean’s ear. “Couldn’t believe I made through to winter break without laying a hand on you. You have no idea how well-formed you are for a shop teacher.” 

Stifling a chuckle, Dean moans and asks, “Why, the shop teachers at your previous jobs got beer guts or something?” The hand around his cock speeds up and the finger in his ass pushes a little deeper, gently circling inside him. A shudder of pleasure rolls through Dean, breath catching in his chest. 

Cas nuzzles the back of Dean’s neck. “They’re trolls in comparison to your beauty,” Cas praises and Dean can’t help blushing from that more than the fact that he’s with a guy for the first time. 

“Okay, I get it. You’re hot for teach—” Dean doesn’t get to finish what he’s saying, because Castiel’s finger slides deeper inside him—his muscles further giving away to the intrusion—and rubs against something Dean hadn’t been expecting. 

Dean shouts, words mangled, as sparks of electricity fly through him from that one little spot inside. His cock jumps and he almost comes. “CAS!” Dean cries. 

“I told you,” Cas growls, “that that girl hadn’t done it right.” Cas nips at Dean’s ear, sucking his lobe into his mouth. Suddenly Castiel pulls his finger out, and lets go of Dean’s cock. Cas reaches round for the lube, awkwardly applying more to his fingers while half hugging Dean. 

Hand returning to Dean’s cock, Cas sets a steady pace and then there’s the pressure of two fingers pushing against Dean’s hole. For a second it feels like too much and then the fingers slip inside of Dean, Cas kissing his shoulder and neck as he fills Dean and plays with him. The fingers inside of Dean slowly caress this most intimate part of him and for the first time Dean feels Castiel’s hardness pressing against the top of his ass cheeks. 

Cas starts to rock the two of them together as his hands work Dean, cock sliding between them. The history teacher was right: Dean hadn’t been fingered properly before and now he was wondering why he’d left it so long to find out how good it could be. Castiel’s fingers stroke against Dean’s prostate again as his hand speeds up on Dean’s cock. 

“Damnit, Cas, gonna, shit, gonna come. Fuck, Cas!” Dean cries, heart racing, body on fire. 

“Come for me, Dean,” Cas growls, hips rutting against Dean. 

“FUCK!” Dean shouts, coming hard as Castiel’s fingers touch him just right again. Cas shouts something into the meat of Dean’s shoulder while Dean coats his hand and Cas coats Dean’s back. 

Dean can’t help whimpering when Cas finally slides his fingers out, hole sensitive in a way it’s never been before. The history teacher unwinds from Dean and cleans the two of them both up before settling back down into the bed again. 

Facing each other, they share slow lazy kisses until they fall asleep in each other’s arms, Dean’s face resting on Castiel’s chest. Dean’s still there once morning comes.

**Author's Note:**

> Kudos and comments appreciated.
> 
> Find me on Tumblr at [dreamsfromthebunker](http://dreamsfromthebunker.tumblr.com/).


End file.
